If Richard Branson has nine lives, he's on at least his fourth or fifth. He has attempted to navigate the Atlantic in a powerboat, cross the Pacific in a hot air balloon and leap into thin air on a skydiving expedition. The boat sank, the balloon caught on fire and, during his skydiving freefall, Branson pulled the wrong releas e tag, jettisoning his parachute. He's a high roller gambling with the biggest stake of all: his life. Yet somehow he always comes out alive--and ahead. He's not only the closest thing we have to a real James Bond, he's also living proof that big risks do pay off. Parlaying his daredevil approach for life to the business world, he's built the Virgin brand to encompass approximately 200 companies spanning dozens of countries and industries, and a net worth valued at $5 billion.

So it's fitting that I'm scheduled to interview Branson, 58, on the southern tip of Manhattan, moments before he announces that he'll be attempting to set yet another world record. This time, he's sailing across the Atlantic. The time to beat: six days, 17 hours, 52 minutes and 39 seconds. His transportation of choice: a 99-foot Super Maxi yacht sporting the Virgin Money brand on its sweeping sails. (Having just forged into the U.S. financial services industry last year, Branson couldn't pass up the strategic opportunity to create some buzz around the new brand.) Icebergs, severe temperatures and 3,000 miles await, and in true Branson style, the departure time is designed to coincide with hurricane winds. "We're about to head off, we're looking for a hurricane to come behind us, and we're going to see if we can be the fastest people to cross the Atlantic," says Branson, who is dressed casually in red-and-white sneakers and a blue collared shirt tucked into jeans, but will soon change into Virgin-branded sailing clothes for the upcoming press conference. Not to be missed is his trademark all-encompassing Branson smile. For the first time ever, Branson will be racing against time accompanied by his two children, Holly, 26, and Sam, 23. And because Branson is Branson, the world is poised to watch.

As I sit on a bench in the shadow of this iconic entrepreneur who first entered the scene big-time with Virgin Music in the ?s and has stayed in the spotlight ever since with airline, rail and soon-to-be space travel brands, I ask what scares him. If his family's health or well-being were ever compromised, that would scare him, he responds immediately. As for his own numerous brushes with death, the sense of fear is fleeting: Cheating death becomes just another challenge. "There are moments when things have gone wrong in adventures where I've certainly been scared," he says. "But equally, I've realized that just like in business, I have to stay completely focused. I haven't got the time or the energy to spend getting scared."

It's with that same disregard for fear that Branson has charged into some of the greatest business challenges to face any entrepreneur. Take the early ?s, when he defied British Airways, which was trying to bar his then relatively minuscule transatlantic airline, Virgin Atlantic, from operating out of Heathrow Airport in London. Reaching ever higher, he has set his sights on a new mission: commercializing space travel. When Branson learned that his neighbor, Microsoft co-founder Paul Allen, had developed the technology to build the world's first privately funded, reusable space vehicle, he immediately envisioned the possibilities. It was that day, says Alex Tai, director of Virgin Group, that "a couple of billionaires sat there discussing how they could push mankind's future into space."

Saying "yes" when others would say "no way" has become Branson's signature trait, and it earned him the nickname "Dr. Yes" from his employees. Says Tai, "He likes to set very high standards for himself and push himself as hard as he can." A gift for accurately sizing someone up in 30 seconds enables Branson to surround himself with a highly talented group of more than 50,000 employees. And his insatiable desire to learn--from life, not textbooks (Branson dropped out of school at the age of 16)--has driven him forward as a serial entrepreneur for more than four decades.

Just as he has always reached high, he pushes his employees to do the same, strongly believing in promoting from within. Tai started out as a pilot for Virgin Atlantic and now, 14 years later, is a crucial player in Virgin Group. Asheesh Advani (Entrepreneur.com's "Startup Financing" columnist), an innovative entrepreneur who founded social lending firm CircleLending, got a call one day from Branson, who was dog sledding in Alaska. Soon after, Branson bought CircleLending, Advani became president of Virgin Money in the U.S., and Branson entrusted Advani to grow the company. "He makes investments and says, 'I want you to grow the business. Here are some guidelines--run with it,'" says Advani. "It's liberating." With this kind of empowering trust, the backing of a killer brand and the right tools, Virgin Money's loan volume soared from $200 million to $350 million in less than a year.

While humankind is generally programmed with an instinct to survive, Branson is wired with an instinct to conquer. "I'm someone who loves to live life to its fullest and doesn't want to waste a minute," says Branson, whose new book, Business Stripped Bare, was just released in September. "I want to make a difference, don't want to waste the position I find myself in and don't want to waste the resources I've got."

Something in his genetic makeup inspires him to constantly push himself to the limits. "He just bought an island next to his current island in the Caribbean, and he and his daughter swam to it," says Tai. "It took them over an hour to swim to the island, but that's the sort of DNA you have in the Branson blood."

Lifting him to new heights is his group of dedicated employees--including his 12th employee ever, who still works for Virgin decades later. Branson's team and his family are also essential to keeping him grounded. As for the day his skydiving expedition nearly became fatal, fortunately there were others around him who responded quickly and were able to activate his reserve parachute, sparing his life. As exhilarating as it is to fly at high altitudes and move through life at lightning speeds, every entrepreneur--especially one as bold as Branson--should have a solid team ready to pull the reserve, if needed.

Reporter's Notebook

8:30 a.m: When I arrive at the harbor, the Virgin Money yacht is swarming with CBS cameramen. The day is promising to be a beautiful one, and there's energy in the air. The press conference is scheduled for 10 a.m.

9:05: As Branson's making his way off the boat to meet me, he's surrounded by people trying to get a minute of his time. He is directed to me, we shake hands, and we head to our photographer, who wants to get a couple of shots in while the light is good.

9:15: It's time to talk. We grab a bench.

9:16: He's midsentence when a passerby introduces herself and asks to take a photo. The woman hands over her contact information and is finally on her way. Branson bids her farewell with a "Cheers."

9:19: We get to talking about his upcoming expedition, how he was raised, and his approach to life and business. As he ponders questions, he squints a little more and smiles a little less, but even at his most serious, his natural expression is that of a smile. His face bears the lines of someone who has spent a lifetime smiling--or of leaning head-on into the wind.

9:30: He's rushed off to get changed and miked for the press conference. He is stopped along the way by a man who inexplicably wants him to sign a life-size cutout of Austin Powers. Branson graciously obliges and then disappears into his yacht.